


The Road to Dean Winchester

by Fangirling_FTW



Series: Destiel One-Shots [26]
Category: Supernatural
Genre: Angst, Angst with a Happy Ending, Dean in Panties, F/M, Homophobic Language, John Winchester's A+ Parenting, M/M, Mentioned trauma, POV Dean Winchester, idk what to tag, mentioned sex, stream of conciousness
Language: English
Status: Completed
Published: 2019-01-23
Updated: 2019-01-23
Packaged: 2019-10-14 22:34:39
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 1,902
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17517086
Author URL: https://archiveofourown.org/users/Fangirling_FTW/pseuds/Fangirling_FTW
Summary: The world wants you to be something.It wants you to fit its mold.But no matter how hard you try... you’re still you.And that’s more than enough.





	The Road to Dean Winchester

**Author's Note:**

> TW// John being a homophobic dick  
> ***
> 
> So this is weird and not my style and idk where it came from but I’m just so happy I WROTE something T-T
> 
> Anyways please leave me comments with encouragement or suggestions I’m ngl I’m kinda not sure about this one :)

Dean is just hitting puberty.  Life is getting confusing all on its own.  Not to mention he keeps overhearing things.  Things he doesn’t quite understand.

“ _ See those lips?  Almost feminine.” _

_ “He’s too pretty for a boy.” _

_ “It’s not fair, he has better eyelashes than me.” _

_ “Such a narrow waist, bet he’d look good in a skirt.” _

Dean’s curious, he’s not gonna lie.  He’s spent hours looking at himself in the mirror, trying to see what they see.  The eyelashes, the body shape, the pouty lips. He wonders if he should feel upset.  He starts to spend too much time in the bathroom, enough that his dad notices. After a lecture about  _ wussy shit  _ Dean makes sure he stops spending that time in the bathroom.

At least when John was home.

 

 

A year progresses, his shoulders widen, his voice deepens and some of the comments stop.  He’s able to ignore the whispers better, stops thinking about it as much. John makes him join the football team.  Dean learns a little about the sport and a lot about the cruel humor found in the boy’s locker room. According to John it’s “ _ just how sports is.” _

Dean doesn’t complain again.

 

 

He has a few girlfriends.  He doesn’t care much for them, but it’s expected of a young attractive boy, so he goes out to pointless dinners and horrible movies.  Kissing is good. Touching is better. Exploration and discovery. It’s something he’s good at anyway. One of the girls is bold enough to take his virginity.  The boys celebrate, but Dean feels a little...hollow.

None of the girls stay for very long.

“ _ He’s too pretty to be straight, he’s gotta be gay.” _

_ “I can’t date a guy prettier than I am.” _

Dean doesn’t mind it, being alone.  He has Sam after all.

 

 

Senior year, a few weeks before graduation and another girl in his bed.  He doesn’t remember her name, and she won’t be around long enough for it to matter.  His dad comes home unexpectedly, so she takes off out the window in her shirt and a pair of his sweats.

Without her skirt or her underclothes.

Dean moves fast, tucking them away, planning on giving them back.  She dumps him at school two days later. Dean leaves them in his closet, hidden from view but insistently on his mind.

Pulling on his jeans after practice, he imagines pulling them on over the panties.  A girl walks by in a similar skirt, he wonders what it would feel like. Another girl tugging on a bra strap tugs Dean’s mind to the back of his closet.  A secret eating him alive, his skin crawling.

_ Does he dare? _

 

 

It takes him two months, but he dares.

His dad is out of the house for the weekend fishing with his friends, and Sam is staying at a friend’s house.

The panties are a little snug, but the soft fabric feels good against his skin.  The skirt is a bit short on him, but it isn’t like anyone is going to  _ see  _ him like this.  The bra is a weird sensation, but it cups his pecs the way it would cup breasts on a girl, and the lace tickles in a nice way across his nipples.

He’s standing in front of the mirror, but he doesn’t want to look away from his own face, flushed bright red and eyes wide.  He takes a deep breath, and he looks.

He feels... _ beautiful.   _ He knows it’s not a word associated with being manly, but he feels it.  The cut of the cotton skirt gives him the illusion of curves, and the pink lace of the bra is delicate against his skin.  He lifts the skirt, and the glimpse of himself wrapped in the panties brings a deeper flush to his cheeks and he lowers it again.  He looks back up at his own face.

He’s smiling.  He  _ loves _ it.

He’s never felt this comfortable in his own skin before.  It’s not that he feels like a girl, but he likes the good feeling the girlish clothes give him.

A flash catches the corner of his eye.  Startled, he hurries to the bed and wraps a blanket around himself.  Laughter drifts in through the window. To his utter horror he discovers part of his blinds didn’t shut all the way.  Peeking out the window, he watches two of his teammates running down the sidewalk.

One of them has a Polaroid.

Dean tears the clothes off, the fabric literally shredding as he pulls it from his body and shoves it in his trash can.  He tugs on a pair of jeans and hurries out to the collection bin, shoving the bag in and hurrying back inside.

Tears sting his eyes, shame and doubt and panic a cold vice on his stomach.  He knows the cruelty of those boys has a sharp edge.

 

 

Photocopies of the pictures arrive in their mailbox a week later.  Dean swears John is going to kill him, he might actually prefer it to the words John is saying.  

_ Faggot.  Pussy. Cock sucker.  Disappointment. Disowned. _

Dean packs his things and says goodbye to his brother, leaving the house for the last time.

 

 

He doesn’t graduate.  He doesn’t speak to Sam for four years.  He travels from place to place, motel to motel, and he buries that night deep, deep down.  When the memories surface, he fucks or drinks them away.

It’s not who he is.  It was all a lie.

He’s the poster boy for masculinity.  Buys a muscle car and fixes it himself.  His nights are spent alone or in the arms of a female stranger.  He works in bars, garages, even takes a turn as a bouncer. He grows up and leaves his  _ phase  _ behind him.  All it brought him was pain.

Sam turns 18 and they start talking again.  Left the house same as Dean, headed out to California.  Dean promises to job hop out west as soon as he can. Neither of them mentions... _ before _ .

 

 

He makes it out west, and he makes some friends, Benny, Charlie, Ash, Pamela.  They become good friends, the kind Dean can trust. But he never talks about his past.  Charlie comes the closest, but all she gets from him is  _ asshole of a father. _  She leaves it alone after that.

 

 

He meets Castiel at a club he takes a job at.  He gets to know him, and suddenly he’s spiraling into him.  The man is taking over his thoughts. Dean shows up to work when he’s not working to see him.  He lets Castiel buy him drinks. He buys Castiel a few drinks. They go out to dinner at one of Dean’s favorite pubs.  It’s not a date. Is it? 

Castiel is a walking contradiction.  Castiel who wears suits to a nightclub, then parties like someone who wouldn’t be caught dead in one.  Castiel who’s quick witted and funny, but who misses out on 90% of Dean’s pop culture references. Castiel who has shoulders and biceps any man would be envious of, but a waistline and an ass any woman would kill to have.  Dean doesn’t like the contradiction, it brings up memories. Memories he thought he’d buried.

 

 

Castiel takes his turn asking about Dean’s past.  Dean wants to tell him, and it’s a terrifying thought.

Dean lashes out, but Castiel isn’t scared away.  He says he doesn’t want to see him, Castiel calls him out on his lie.  He quits his job, but Castiel blows up his phone.

Castiel wants him.  But he  _ wants  _ Dean, and Dean can’t because Castiel is a man.  Thoughts and emotions haunt him until he drinks them into submission.

Dean hurts.  But not a physical ache.  An ache that leaves him feeling like he’s barely hanging on.  He carries himself carefully, puts a mask on in front of people and almost never takes it off.  Castiel is tugging on it, trying to rip it off where it’s glued onto Dean’s skin. He’s torn, bloody and broken. 

He wants Castiel, but he doesn’t want Castiel to see him.  Not like this, when he deserves someone much better, much less damaged.

It’s better this way.

 

 

In the end it’s all because of an accident.  

They’re both in the snack aisle at the grocery store, unexpectedly face to face.  It’s awkward, uncomfortable. Castiel tries an apology. Dean wants to throw it back in his face.

A bag of Doritos falls to the floor instead, dropped from Dean’s hands.  Dean abandons everything he’s tried to build to protect himself. Hands are gripping Castiel tightly, begging him to save Dean, to stop the bleeding.  He feels guilty for asking, surely it’s too much. 

 

 

Weeks go by.  Castiel assures him it’s not too much.

 

 

The first time they have sex Dean cries and runs out of the room.  Castiel waits by the bathroom door until he comes out. He assures him again, it’s not too much.

 

 

A year passes.  A set of apartment keys.  It’s not too much, it’s...enough.

 

 

Some more months, some fights.  Castiel knows Dean is holding something back, and he’s pushing.  He pushes so hard it pushes Dean away for a few days. Dean finds an old friend in alcohol.  He finds a bed at Charlie’s. After some time when Dean is sure it’s the end, still Castiel is there.  They talk, and it’s enough. It’s enough.

 

 

Dean’s staring down a second anniversary, something new for him.  Suddenly...it’s not enough. It’s not enough because Castiel is part of him now and he needs him to know.  He needs to know if, even after all this, Castiel is telling the truth. That it’s  _ really _ not too much.

So he calls his best friend, and she doesn’t ask questions.  Charlie helps him with so much more than what he asked for. Dean didn’t even realize just how little he was fooling anyone.

 

 

It’s the night.   _ The  _ night.  He’s nervous, anxious, nauseous.

Castiel comes home.

Dean’s never seen his blue eyes go that wide.

A form fitting black skirt, a sky blue blouse.  Castiel doesn’t run away. Soft words, an exclamation of wonder.  Dean tried to explain, but Castiel knows. The puzzle pieces fall into place and Castiel knows what he’s trying to say.  More soft words, confirmation that Castiel is here to stay.

Permission is given.  Greedy hands and loving touches filled with adoration strip Dean of more than just his clothes.  

A matching set, black lace bra and panties.  Dean’s masculinity wrapped up in something dainty and feminine.  Dean wants to run away again, but Castiel’s hands, his words, his eyes keep him there.  

They make him feel  _ beautiful  _ again.  Just like the first time.  He doesn’t squash the memories, he doesn’t bury them.  He  _ remembers _ .  

Dean’s never felt this level of physical or emotional bliss before.  Making love was just a phrase, but that night Castiel makes it manifest.  Words are exchanged after, long into the night.

 

 

Two years, three months, twelve days.

Dean’s finally himself, and Castiel is right there.  Castiel with his own contradictions, like Dean’s. Castiel who makes Dean want things he’s never thought of.  

It’s not enough.  At least, not until the ring slides into place over Castiel’s knuckle.

 

 

Dean’s closet gets an upgrade, as does his life, and Castiel tells him with his words and his body.  

This, Dean as he was meant to be, is more than enough.


End file.
